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#WellDressed: Men and Kentucky Derby Hats

The Kentucky Derby isn’t just about “The Most Exciting Two Minutes in Sports”—it’s about the famous hats and fashion, too. In 1875, the public viewed horse racing as a place for gambling and drinking. To combat the negative image, the founder of the Derby launched a campaign to attract high society—and a style sensation was born.


So how did Derby hats get so crazy? The decorated fedoras and wide-brimmed hats we see today didn’t garner popularity until the 1960s, when women’s fashions became more carefree and flamboyant. Hat enthusiasm decreased in the ‘70s and ‘80s, but it saw a resurgence in the ‘90s and with the Royal Wedding in 2011 (you remember all of those). Derby hats have been traditionally worn by women for good luck, though in the past few years, men have sported a range of hats, from Homburgs and Panamas to Trilbies and fedoras. Many men and women have their hats custom made, while others choose to add embellishments themselves.

Our Derby attire advice? Be original, have fun, and above all: Don’t forget the hat.

The Tradition:

 Tom Brady


The Extreme:


133rd Kentucky Derby

Article courtesy of Adam Bruk of Fedoras

One Response to “#WellDressed: Men and Kentucky Derby Hats”
  1. Marty Martin says:

    I love it!

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